Virtual Strategic Planning: The Silver Lining

When news of Covid hit about eight months ago (or was it eight years ago?) many of us thought we’d be back to “normal” within a few months. Workers would be returning to offices, groups could meet again in person, and conferences and events scheduled for 2021 could go on as planned. But of course, we were wrong. As the virus continues to spread unabated, organizations are scrambling to rethink their meeting plans for 2021.

Strategic planning has never been needed more, but it can be one of the hardest activities of all to pull off virtually. That’s because it takes several thoughtful conversations where people may be articulating a new vision or mission, establishing goals, setting shared priorities, and mapping out actionable plans. When done in person, strategic planning conversations often take multiple days. When run virtually, the process can span several weeks. Designed thoughtfully, virtual strategic planning doesn’t have to painful or tedious, and it can actually be fun!

Here are some tips for designing, facilitating and guiding a virtual strategic planning process that seamlessly blends asynchronous and synchronous conversations in a way that makes it easy to integrate and synthesize all ideas and ultimately, to agree on priority goals and a concrete plan of action to achieve them.

  • Create an overall roadmap of the process, including all major activities, including objectives by participant group, inputs, outputs and timing. Be sure to include what happens after the final planning workshop, such as the formation of subteams, whose members may be proposing programs and resource requirements and presenting to decision-makers for approval and budget, and any other next steps that begin after the final planning workshop ends.
  • Build a core team of people to help guide the process. Some members may come from your leadership group and some from the broader community. I recommend no more than 5-7 people. This team might meet 2-3 times over the course of the planning effort to help guide and validate the process, sanity-check survey questions, discuss implications of responses, help winnow down the list of strategic priorities, and act as champions of new strategic initiatives.
  • Determine who needs to participate, in what role, at what time, and through what means. You may want broad community representation, for example, when it comes to soliciting ideas, surfacing challenges and seeking other important input. But when it comes to the real-time conversations where priorities are set, decisions are reached and actions planned across a virtual table, you’re likely to be doing this with your designated planning team.
  • Get the timing right. If, for example, you plan to open up online asynchronous conversations to gather input and ideas, give yourself enough time for people to participate. I recommend at least five working days. You also need time to review and synthesize responses as a springboard for your initial planning workshop. I suggest starting with an online asynchronous conversation, followed by at least two to three facilitated real-time planning workshops, with “homework” of some kind in between. This might take the form of online voting, brainstorming, idea-building or action planning. I suggest allowing at least 10 days between virtual planning workshops, to let ideas percolate.
  • Cast a wider net through asynchronous conversations. One big advantage of working virtually is that we can invite a broad cross-section of the community into the conversation for minimal additional cost. (I’ve found that since the pandemic, people have been enthusiastic about joining these online conversations when they believe their perspectives can make a difference.) Other keys to conducting a successful online conversation: Ask questions that are clear, relevant and easy to answer. Limit the time needed to complete responses to no more than about 15 minutes. Determine whether responses will be attributed or anonymous. (I typically recommend including the names of respondents, so people feel like they are actually having a conversation with someone, and this also makes it easier to gauge interests and follow up. If you feel that you might get more honest responses if certain questions are anonymous, make sure to use a tool that gives you flexibility.)
  • Assemble a team to help plan and run your virtual workshops. It really does take a village. You’ll want someone who can help with the technology. (For example, I often use Zoom for audio/video and chat and another tool where people can capture ideas to debrief and save for later.) You may need a note-taker, either for the whole workshop or for breakout groups, depending on whether people will be capturing ideas as they go. Timekeepers can be essential, as are those who keep an eye out for chat responses, raised hands, or questions that the workshop facilitator may miss. If visuals of some kind are needed, determine who is responsible for creating and assembling the content. Finally, agree on who will be kicking off and closing out each workshop; ideally, this will be the “owner” of the strategic plan.
  • Divide your conversations into chunks, by objectives. Consider which objectives you can realistically achieve in a single virtual planning workshop, what kind of conversations are needed to accomplish each one, and where and when those conversations need to take place. I usually limit each planning workshop to no more than two hours, with a brief break at the halfway mark. Keep in mind that it’s almost impossible to have a true conversation with more than 6-7 people at a time, so consider breakout groups to foster deeper conversations and generate ideas more quickly. Allocate time for debrief and group reflection. For larger group conversations, use chat and other features of your meeting app to enable more contributions from more people. And remember: Some conversations can occur asynchronously between planning workshops.
  • Keep people engaged. Here are a few quick tips: Help people come to the session geared up to participate by letting them know in advance what kind of contributions you’ll be asking for and how they can best prepare. Resist the temptation to invite everyone you can think of, and limit the virtual planning workshops to no more than about 15 people or so. Establish meeting norms regarding participation and revisit at least a few at the start of each session. Use at least two forms of communication to gather all ideas, questions and comments, in writing and verbally. Use breakouts to get people talking, even if they must be super-brief. Be ready with stimulating questions that will inspire everyone to lean in, rather than sit back. Vary activities every few minutes so people are less likely to zone out or lose interest.
  • Have a plan for balancing participation and managing difficult behavior. Knowing something about your participants can help, but it isn’t critical. What is important is to anticipate what kinds of behavior might be most likely to block progress, and to have a plan to manage it diplomatically, yet assertively. Having a set of closed-ended questions to spark conversation and shift the energy can be a lifesaver in handling many tough situations.
  • Define next steps before you start the first step. (See Roadmap) Make sure the owner of the planning process feels accountable for implementing the results. I usually recommend that subteams be created to create proposed plans that support strategic priorities, which can then be presented to decision-makers for a go/no-go decision. The plan’s ultimate owner needs to have thought through how plans will be implemented, and just as important, what can be taken off the plates of busy people to bring these strategic priorities to life. If you believe there is no such commitment to implementing the results, you might want to question the wisdom of embarking on this journey until a plan can be put into place.

Strategic planning is not the same as business planning, where organizations typically validate or tweak their current plans but for the most part, don’t deviate significantly from the status quo. True strategic planning involves looking for breakthrough opportunities never before imagined that can significantly change the trajectory of the organization for years to come. It calls for eliciting new ideas from a diverse stakeholder community, followed by a series of thoughtful conversations to determine which ideas, if implemented, will position organizations more strongly in the future, and for creating a realistic plan of action to bring new ideas to life. (It also usually means having to declare what your organization will no longer do.) Thanks to our ability to collaborate and communicate across time and distance, we have new ways of designing and running productive strategic planning conversations, involving more perspectives than we ever imagined possible. There’s never been a better time to start.


Examples from Guided Insights

Strategic Planning Sample Timeline of Activities

Strategic Planning Process for Nonprofit Board – visual

Past Communiques:

Create a 12-Month Plan in Just Two Hours, With a Little Bit of Magic

Moving from Ideas to Action in a Virtual World

When Collaboration Becomes Way Too Much of a Good Thing

Links to other articles:

Your Strategic Plans Probably Aren’t Strategic, or Even Plans – Harvard Business Review, 2018


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